Hydrochloric Acid → 4-Bromo-3-methylbenzaldehyde

HRID 1741069Notes

Reaction equation

HRID 1741069 reaction equation
CON(C)[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:13])=[CH:6][C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 218337954-bromo-N-methoxy-N,3-dimethylbenzamide

Product 1

HCID 109215214-Bromo-3-methylbenzaldehydeYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methoxy-N-methyl-4-bromo-3-methylbenzamide (D17) (12 g; 0.046 mol) in dry tetrahydrofuran (120 ml) under argon, at -78° C. was treated dropwise over 15 minutes with diisobutylaluminium hydride (1.5 m in toluene) (46 ml; 0.069 mol). After a further 15 minutes the reaction mixture was added to 5N HCl (100 ml) and extracted into diethyl ether. The organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a red oil (8.98 g, 97%).

Workup

  1. extractionextracted into diethyl ether
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9ba459be13e840e1bc4e7ed7b635ca61
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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